Reflection is of increasing interest in HCI as it has many potential benefits in design, education and everyday life. In this paper, we explore media-supported reflection through the design and deployment of three concepts. In contrast to prevalent reflective approaches that are based on system-collected data, we explore how user-created media can support personal reflection. Three interactive prototypes were developed, focusing on different modalities: Balance uses audio, Cogito uses text, and Dott uses visual media. We evaluate these concepts in an inthe-wild study that is both explorative and comparative. We found that the open-ended systems primarily supported reflection during the creation of media and that the use depended on opportunity and triggers. We conclude the paper with a discussion of our findings regarding the method and the implications of our findings for the broader area of design for reflection.